'Whitey' Bulger faces off with FBI agent who went from pal to prosecution witness

By Deborah Feyerick and Kristina Sgueglia, CNN

Updated 1151 GMT (1851 HKT) June 28, 2013

Who's who in the James 'Whitey' Bulger case23 photos

Who's who in the James 'Whitey' Bulger case – James "Whitey" Bulger, the former head of Boston's Winter Hill Gang, evaded police for 16 years before his 2011 arrest with girlfriend Catherine Greig in Santa Monica, California. After a lengthy trial, Bulger, seen here in his booking photo from June 23, 2011, was found guilty on 31 of 32 counts -- including involvement in 11 murders. On November 14, 2013, Bulger was given two life sentences plus five years. Here's a look at some of the people tied to Bulger's life of crime:

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Who's who in the James 'Whitey' Bulger case23 photos

Who's who in the James 'Whitey' Bulger case – James "Whitey" Bulger, seen here in a 1984 FBI photo, spent nine years in federal prison before he climbed the ranks of the Winter Hill Gang -- the preeminent Irish-American crime syndicate in the Boston area -- in the early 1970s.

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Who's who in the James 'Whitey' Bulger case23 photos

Who's who in the James 'Whitey' Bulger case – According to prosecutors, Bulger's crew learned that a bookie named Richard Castucci was cooperating with the government, and John Martorano was sent to kill him. Castucci was shot in the head in December 1976 and stuffed in a sleeping bag in the back of his car.

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Who's who in the James 'Whitey' Bulger case23 photos

Who's who in the James 'Whitey' Bulger case – Steve "The Rifleman" Flemmi, left, and bookie Dick O'Brien in one of several surveillance photographs entered into evidence in the Bulger trial. Flemmi, Bulger's partner, would meet O'Brien to collect thousands of dollars in "rent" every month.

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Who's who in the James 'Whitey' Bulger case23 photos

Who's who in the James 'Whitey' Bulger case – Bulger is accused of murdering Flemmi's stepdaughter, Deborah Hussey, in 1985 because she became a liability.

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Who's who in the James 'Whitey' Bulger case23 photos

Who's who in the James 'Whitey' Bulger case – Flemmi met Debra Davis at a jewelry store, and the couple dated for more than seven years. In 1981, Bulger is said to have killed Davis because she knew that Flemmi was an informant.

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Who's who in the James 'Whitey' Bulger case23 photos

Who's who in the James 'Whitey' Bulger case – Dr. Ann Marie Mires, a Massachusetts state forensic anthropologist, was brought in to Bulger's trial show photos of his alleged victims, including Debra Davis. Because Davis' body was put into bags, almost all of her remains were recovered. Even some of her hair was preserved.

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Who's who in the James 'Whitey' Bulger case23 photos

Who's who in the James 'Whitey' Bulger case – Mug shots of Bulger in 1953, about a year after his honorable discharge from the U.S. Air Force.

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Who's who in the James 'Whitey' Bulger case23 photos

Who's who in the James 'Whitey' Bulger case – Bulger was the godfather to John Martorano's first son. Martorano has admitted to 20 killings as part of Boston's Winter Hill Gang and was the government's star witness against Bulger.

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Who's who in the James 'Whitey' Bulger case23 photos

Who's who in the James 'Whitey' Bulger case – In 2008, John Martorano, pictured here, testified against former FBI agent John Connolly, who was accused of leaking sensitive information about former gambling executive John Callahan. Martorano testified that he shot his friend Callahan on Bulger's orders in 1982.

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Who's who in the James 'Whitey' Bulger case23 photos

Who's who in the James 'Whitey' Bulger case – John Callahan was an organized crime associate of the Winter Hill Gang and former president of World Jai Alai. Prosecutors allege Bulger ordered a hit on Callahan after he learned he would be cooperating with the feds on the high-profile murder of an Oklahoma businessman, Roger Wheeler.

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Who's who in the James 'Whitey' Bulger case23 photos

Who's who in the James 'Whitey' Bulger case – Bulger is accused in the slaying of Wheeler, who was gunned down outside a country club in Oklahoma in 1981.

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Who's who in the James 'Whitey' Bulger case23 photos

Who's who in the James 'Whitey' Bulger case – Joe Notorangeli was gunned down by the Winter Hill gang in 1973, according to Martorano.

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Who's who in the James 'Whitey' Bulger case23 photos

Who's who in the James 'Whitey' Bulger case – John Connolly was convicted of second-degree murder in the slaying of Callahan and received a 40-year sentence in 2009. A Florida appeals court vacated that conviction in May 2014, citing a statute of limitations issue. Connolly remains incarcerated as prosecutors try to convince the appeals court to reverse its decision.

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Who's who in the James 'Whitey' Bulger case23 photos

Who's who in the James 'Whitey' Bulger case – Former FBI supervisor John Morris testified at Bulger's trial that he provided information to Bulger in exchange for money and gifts. Here, Morris testifies during the John Connolly murder trial in Miami in 2008.

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Who's who in the James 'Whitey' Bulger case23 photos

Who's who in the James 'Whitey' Bulger case – Bulger's girlfriend, Catherine Greig, was sentenced to eight years in federal prison in 2012 for identity fraud and helping the reputed mob boss avoid capture for 16 years.

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Who's who in the James 'Whitey' Bulger case23 photos

Who's who in the James 'Whitey' Bulger case – J.W. Carney, Bulger's defense attorney, arrives at the U.S. Federal Courthouse for the start of Bulger's trial in Boston on Wednesday, June 12, 2013.

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Who's who in the James 'Whitey' Bulger case23 photos

Who's who in the James 'Whitey' Bulger case – This undated surveillance photo released by the U.S. Attorney's Office in Boston shows Bulger, left, with his former right-hand man, Kevin Weeks. Weeks took the witness stand at Bulger's racketeering trial and described a double slaying, multiple extortions and drug dealing.

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Who's who in the James 'Whitey' Bulger case23 photos

Who's who in the James 'Whitey' Bulger case – Bulger and Kevin Weeks walk around Castle Island on Boston Harbor.

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Who's who in the James 'Whitey' Bulger case23 photos

Who's who in the James 'Whitey' Bulger case – Kevin Weeks leaves the courthouse in July 2013 after testifying in graphic detail about how Bulger killed Arthur "Bucky" Barrett, Joey McIntyre and Deborah Hussey.

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Who's who in the James 'Whitey' Bulger case23 photos

Who's who in the James 'Whitey' Bulger case – The remains of Thomas King, former member of the Winter Hill Gang, were found in late 2000 and included these driving gloves, a bulletproof vest, a navy suit, and a claddagh ring. Martorano, one of Bulger's hitmen, testified that he himself had shot King in the back of the head.

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Who's who in the James 'Whitey' Bulger case23 photos

Who's who in the James 'Whitey' Bulger case – Stephen Rakes, 59, was scheduled to be a witness for the prosecution before he was dropped from the list. His body was found July 17, 2013, in Lincoln, Massachusetts, west of Boston. Rakes' business associate has been charged with his murder. Authorities said Rakes' killing was unrelated to the Bulger case.

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Who's who in the James 'Whitey' Bulger case23 photos

Who's who in the James 'Whitey' Bulger case – Trying to show a softer, lighter side of Bulger, his defense lawyers released numerous photos of their client during the 2013 trial. The tactic didn't work: Bulger will spend the rest of his life in prison.

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Story highlights

A former FBI agents is asked: "You were corrupt, weren't you?"

"Yes," comes the answer from agent, who is testifying against "Whitey" Bulger

Reputed mob boss Bulger is charged with 19 murders

He lived in hiding for 16 years, after a tipoff from an FBI source that he faced indictment

Reputed mob boss James "Whitey" Bulger, visibly annoyed, muttered under his breath "You're a f---ing liar" Thursday as a disgraced former FBI supervisor testified that there was "no question" the Irish gangster doubled as an informant for FBI Boston.

Both sets of attorneys have spent a remarkable amount of time during the trial of the notorious Bulger, charged with 19 murders and in court after living in hiding for 16 years, trying to prove whether Bulger was an informant during a 15-year period. Even Judge Casper is beginning to question the importance of the issue.

During post-court discussion over motions, as the defense was attempting to further it's argument that Bulger's informant records were forged by his FBI handler, Judge Casper questioned, "How does that address that your client is not guilty of crimes here?"

Bulger's attorney J.W. Carney danced around the question and responded, "Bulger was not providing information as an informant, he was providing money so that he'd get tipped off about wire taps and search warrants."

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Bulger's attorneys have been quick to admit to acts of extortion and racketeering -- charges Bulger is also facing -- to defend their client's position that he was not another "rat" from South Boston.

"Why can't both be true?" Judge Casper inquired.

"The defendant's position is (that) only one is true." Carney said. "Why would James Bulger be paying all this money to all these people if the government's theory is he got all this protection because he was providing information. Why would he keep paying everybody?"

Former FBI supervisor John Morris, an addition to the government's long list of cooperating witnesses, testified Thursday that he took bribes from Bulger in the amount of $7,000, along with a silver-plated champagne bucket and two cases of imported wine.

Morris said he asked Bulger if he could "spring" for a plane ticket for his secretary girlfriend to visit him during FBI training in Georgia, and Bulger obliged. Morris admitted to his acts of corruption in 1997 in exchange for immunity.

A sheepish, red-faced Morris, though less than six feet away from Bulger, avoided eye contact with the defendant, who glared steadily at his old confidant throughout his testimony. This is the first time the two have seen each other since they cut ties in 1991 after Morris leaked Bulger's informant status to the Boston Globe.

Morris said he first met Bulger at a dinner he hosted his Lexington, Massachusetts, home in 1978 along with Bulger's FBI handler John Connolly, whom he characterized as his "best friend."

Morris said he met Bulger and later his associate Steve "The Rifleman" Flemmi eight to 10 times in various places, including Morris' home, Morris' girlfriend's apartment, a hotel, Bulger's home and even in Flemmi's mother's house for dinner. Flemmi's mother cooked. The defense has previously argued that Bulger was not treated like an informant, and thus did not believe that he was.

Morris testified that Connolly preferred to meet Bulger in "pleasant surroundings, not the type of surroundings you would meet a normal informant," like in a hotel or car. "He wanted Mr. Bulger to be comfortable," Morris said.

Morris was supervisor to rogue FBI agent Connolly, who is currently serving a 40-year sentence on second-degree murder charges for leaking the identities of witnesses cooperating against Bulger's Winter Hill Gang. Flemmi, serving a life sentence, is set to testify against Bulger later in this trial after agreeing to cooperate with the government to evade the death penalty in 1997.

All that Bulger and Flemmi wanted from their handlers in exchange for information was "a head start," as Morris described -- to be tipped off if they were going to be indicted or charged so they could flee. The pair, according to Morris, knew they were "fair game" and acknowledged that they were engaging in criminal activity and at some point they might get charged. If that happened, they didn't want their identity as informants disclosed and would rather "take the risk" Morris said.

Morris admitted to tipping his informants off to wire taps, and keeping their names out of a 1975 horse race indictment. He testified that the Mafia, or La Cosa Nostra, was the main priority of the FBI in Boston and that Bulger and his partner Flemmi were instrumental in the take-down of those mobsters. The two provided the agents with a drawing of Mafia headquarters, and that was used to take down the New England Mafia in a 1983 sting.

After being tipped off to an indictment, Bulger went on the run for 16 years and landed himself on the FBI's top 10 most wanted list before being arrested in his Santa Monica. California, home with his girlfriend in 2011.

Morris said that he signed off on reports Bulger provided to the FBI that he knew were false lies to protect himself from being implicated as the person to who leaked sensitive information that may have tipped Bulger off to witnesses that were cooperating against him. Those potential witnesses were eventually murdered, Morris said, and Bulger has been charged in their killings.

While the defense had little time to cross-examine Morris, who will be back on the stand Friday, defense attorney Hank Brennan painted Morris to be a liar, an adulterer, and a fraud. He was able to fire off a question that is likely to resound with the jury.